878-55-7

Basic information

• Product Name: 4,4a,5,6,7,8-Hexahydro-1,4a-dimethylnaphthalen-2(3H)-one
• Synonyms: 4,4a,5,6,7,8-Hexahydro-1,4a-dimethylnaphthalen-2(3H)-one;1,4a-diMethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one;1,4a-Dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one
• CAS NO: 878-55-7
• Molecular Formula: C₁₂H₁₈O
• Molecular Weight: 178.2707
• Mol File: 878-55-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 275°Cat760mmHg
• Flash Point: 114.7°C
• Appearance: /
• Density: 0.99g/cm³
• Vapor Pressure: 0.00521mmHg at 25°C
• Refractive Index: 1.502
• CAS DataBase Reference: 4,4a,5,6,7,8-Hexahydro-1,4a-dimethylnaphthalen-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4a,5,6,7,8-Hexahydro-1,4a-dimethylnaphthalen-2(3H)-one(878-55-7)
• EPA Substance Registry System: 4,4a,5,6,7,8-Hexahydro-1,4a-dimethylnaphthalen-2(3H)-one(878-55-7)

Safety Data

• Hazardous Substances Data: 878-55-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 108, p. 304, 1986 DOI: 10.1021/ja00262a025Synthesis, p. 608, 1977 DOI: 10.1055/s-1977-24493

InChI:InChI=1/C12H18O/c1-9-10-5-3-4-7-12(10,2)8-6-11(9)13/h3-8H2,1-2H3

Upstream product

• 42991-07-1 2-Triethylsilanyl-pent-1-en-3-one 
• 13670-84-3 2-methylcyclohexanone lithium enolate 
• 1629-58-9 4-penten-3-one 
• 583-60-8 2-Methylcyclohexanone 
• 132680-35-4 (+/-)-3,4,4aα,5,6,7,8,8aα-octahydro-8aα-hydroxy-1β-methyl-2-oxo-1H-naphthalene-4aα-carbonitrile 
• 132680-35-4 (+/-)-3,4,4aα,5,6,7,8,8aα-octahydro-8aα-hydroxy-1α-methyl-2-oxo-1H-naphthalene-4aα-carbonitrile 
• 132680-35-4 (+/-)-3,4,4aα,5,6,7,8,8aβ-octahydro-8aβ-hydroxy-1β-methyl-2-oxo-1H-naphthalene-4aα-carbonitrile 
• 91191-69-4 (+/-)-<1α(Z),4aβ>-1-(3-Chloro-2-butenyl)-3,4,4a,5,6,7-hexahydro-1,4a-dimethyl-2(1H)-naphthalenone 
• 107957-68-6 3-methoxy-2-pentene-1-ol 
• 19980-35-9 1-trimethylsilyloxy-2-methyl-1-cyclohexene 
• 52103-30-7 1-(diethylamino)pentan-3-one methiodide 
• 22104-65-0 N,N-dimethylaminopentan-3-one 
• 32830-97-0 1-chloro-3-pentanone 
• 91-22-5 quinoline 

Downstream Products

• 22515-82-8 1-pentene-3-one ethylene acetal 
• 91191-66-1 (+/-)-2-Ethyl-2-<2-<(3,4,4a,5,6,7-hexahydro-1,4a-dimethyl-2-naphthalenyl)oxy>ethyl>-1,3-dioxolane 
• 878-54-6 (+/-)-4,10-Dimethyl-cis-decalin-3-on 
• 5173-69-3 r-1,c-4a-dimethylperhydronaphthalen-t-8a-ol 
• 5173-65-9 (+/-)-1,10-Dimethyl-Δ¹⁽⁹⁾-octalin 
• 4668-61-5 1,1,4a-trimethyl-3,4,4a,5,6,7-hexahydronaphthalen-2(1H)-one 
• 91191-69-4 (+/-)-<1α(Z),4aβ>-1-(3-Chloro-2-butenyl)-3,4,4a,5,6,7-hexahydro-1,4a-dimethyl-2(1H)-naphthalenone 
• 91191-68-3 (+/-)-<1α(Z),4aβ>-1-(3-Chloro-2-pentenyl)-3,4,4a,5,6,7-hexahydro-1,4a-dimethyl-2(1H)-naphthalenone 
• 878-54-6 (+/-)-1t,4a-dimethyl-(4ar,8at)-octahydro-naphthalen-2-one 
• 878-54-6 (+/-)-1t,4a-dimethyl-(4ar,8ac)-octahydro-naphthalen-2-one 

Relevant articles and documents

Synthesis of (+/-)-Geosmin. Part 1. On the Synthesis and Epoxidation of 1,4a-Dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one

An improved method for the preparation of 1,4a-dimethyl-4,4a,5,6,7,8-hexahydronaphthalene-2(3H)-one has been developed.This compound has been used as a key intermediate in several previous syntheses of geosmin.The regioselectivity in the alkylation of 2-methylcyclohexanone with ethyl vinyl ketone or 1-chloro-3-pentanone was investigated. The stereoselectivity in the epoxidation of the octalone by hydrogen peroxide, t-butyl hydroperoxide and m-chloroperbenzoic acid was also studied.The results obtained were, to some extent, different from previous reports, both with respect to regio- and stereo-selectivity.The isolated yield of the octalone was 81-83percent as a 96:4 mixture with the 1,8-dimethyl isomer.Epoxidation of this material using m-chloroperbenzoic acid resulted in a 92:8 (α:β) mixture of epoxides, which also contained 4percent of the epoxide(s) from the 1,8-dimethyloctalone isomer(s).The isolated yield of epoxide mixture was 89percent.

Deprotonation of Chelating Enamines. Direct Formation of β-Lithio Enamines

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